AI and the Future of Work: Artificial Intelligence in the Workplace, Business, Ethics, HR, and IT for AI Enthusiasts, Leaders and Academics

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Ryan Gavin is Chief Marketing Officer at Slack, the global collaboration platform used by more than 200,000 organizations across 150 countries. Since joining Slack, Ryan has helped drive a 250% increase in revenue while championing the launch of Slack's AI-first capabilities and agentic integrations.

A seasoned technology executive, Ryan previously served as Chief Growth Officer at Convoy and held senior leadership roles at Amazon Web Services and Microsoft, where he managed multi-billion-dollar business units.
In this episode, Ryan draws on watching hundreds of enterprise AI rollouts up close to make the case that dropping agents into an organization without a strategy doesn't just fail to help, it actively backfires.

In this conversation, we discuss:
Why single-player AI tools fail to deliver enterprise productivity gains, and how deploying autonomous agents into collaborative, multiplayer environments unlocks hidden software value.
How a conversational interface connects unstructured team dialogue with structured CRM data, allowing employees to query enterprise systems without opening underlying software tabs.
What the concept of "headless software" reveals about democratizing access to sales and operational insights across non-technical departments.
Why transparent, step-by-step reasoning and strict permission inheritance are essential for building trust when introducing AI tools into enterprise workflows.
How leading organizations elevate Slack from a conventional IT collaboration expense into a core strategic driver for company-wide AI adoption.
What executive advice for emerging professionals highlights the enduring value of curiosity, creativity, and adaptability in a rapidly changing job market.

Explore the conversation
00:00 Show Intro, a Team Human Success Story, and Meet Ryan Gavin
03:44 Ryan Gavin's Path to Becoming CMO of Slack
04:57 Slack's New Job in the Age of AI Agents
07:53 Designing SlackBot to Strengthen Human Collaboration
12:31 Headless Salesforce and Slack as the New Front Door
16:50 Slack as 2% of Your AI Budget and the Problem With 'Work About Work'
21:37 Trust, Transparency, and the AI Black Box in SlackBot
25:28 From Slash Commands to Every Employee as a Builder
31:40 Winning Share of Wallet in a Zero-Sum AI Budget
35:54 Advice for Workers Who Feel Left Behind by AI
39:35 Where to Find Ryan Gavin and Slack

Resources
Subscribe to the AI & The Future of Work Newsletter
Connect with Ryan on LinkedIn
Other episodes mentioned on the show:On How Silvio Savarese, EVP and Chief Scientist at Salesforce, navigated the real challenges of taking AI from the ivory tower to corporate labs (Episode 297)
On How Kai Nunez, Vice President of Research & Insights at Salesforce, shares the secret to making tech teams own responsibility for AI ethics (Season 2, Episode 47)

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See why Freshworks was named a Leader in the 2026 Gartner® Magic Quadrant™ for ITSM. Learn more → freshworks.com/dant

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Kartik Sakthivel is the Chief Information Officer at John Hancock, the life insurer that turned 164 years old in April 2026 and is part of Manulife. Before joining, he spent eight and a half years at LIMRA and LOMA, the oldest and largest trade association in financial services, which gave him a view across carriers few technology leaders ever get. 
Recorded live from the floor of Ai4 2026, this lightning round explores what it takes to bring AI into a company founded during the Civil War, and why he tells his teams that what they build today becomes the legacy for the next 164 years.
Kartik and host Dan Turchin dig into why he believes every technology leader should think of themselves as a business leader first, how a regulated industry decides what to fast track and what to slow down, and what he says to people who are watching a machine learn to do the thing that made them valuable.
What You'll Learn
Why uptime and mean time to repair are table stakes for a modern technology organization, and what Kartik measures instead
How a highly regulated business draws the line between internal AI that gets fast tracked and anything customer facing that does not
Why there are more AI pilots in insurance than planes at a major airport at peak hour, and how to find use cases that are neither too small to matter nor too large to finish
The question he asks every time the business brings him an AI idea, and why the answer is sometimes something far simpler
What he tells colleagues watching automation absorb part of their role, and where the time that comes back should be reinvested

🎙️ Part of our Ai4 2026 compilation series. 
Listen to the full compilation here: https://www.buzzsprout.com/520474/episodes/19816277  

Resources
Subscribe to the AI & The Future of Work Newsletter
Connect with Kartik on LinkedIn

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Cesar Carvalho is the co-founder and CEO of Wellhub, the corporate well-being platform connecting millions of employees to top-tier fitness, mindfulness, therapy, nutrition, and sleep partners across 18 countries. 

Since founding the company as Gympass in 2012, Cesar has raised nearly $900 million in venture funding, reached a $2.4 billion valuation, and grown Wellhub to serve over 50,000 corporate clients worldwide. 

In this episode, Cesar sits down with Dan to discuss why treating employee wellness and business performance as opposing forces is a false dichotomy. Tune in to hear his perspective on why AI should be leveraged to fund employee reskilling rather than justify job cuts, how Wellhub's AI wellness coach scales hyper-personalized care to millions of subscribers, why less than 10% of global healthcare spending goes toward prevention, and how pivoting during the 2020 pandemic transformed a near-death crisis into a multi-product wellness ecosystem.

In this conversation, we discuss:
Why framing corporate wellness as an adversary to business performance is a false dichotomy, and how employee health directly drives bottom-line execution.
How granting employees 30 minutes of paid work time daily to experiment with AI tools fosters a culture of innovation and continuous reskilling.
What the structural imbalance between preventive "well care" and reactive "sick care" reveals about the urgent need to redesign enterprise benefits.
How an AI-powered wellness coach expands personalized fitness and mindfulness guidance from hundreds of thousands to millions of corporate subscribers.
Why strict data minimization policies and phased beta testing provide a trusted framework for deploying AI in sensitive health environments.
What pivoting a global business model during the 2020 pandemic teaches founders about mission alignment, resilience, and turning near-death moments into catalysts for growth.

Explore the conversation:
00:00 Show Intro and Newsletter Shoutouts
02:07 AI Fun Fact: Chatbots and Mental Health Risks
04:01 Introducing Cesar Carvalho, CEO of Wellhub
05:03 From Harvard Dropout to Corporate Wellness: The Founding of Gympass
06:56 The "Team Human" Ethos: Making Well-Being Ubiquitous at Scale
09:14 Performance vs. Health: Why Employee Well-Being Directly Drives Execution
12:37 Calling Out AI Layoffs: Are Employees Expendable?
14:12 Reskilling Over Layoffs: Why Wellhub Invests in Existing Talent
16:34 Personalization at Scale: Expanding the AI Wellness Coach Across Millions
20:19 Responsible AI at Wellhub: Data Minimization and Governance Standards
22:36 Sick Care vs. Well Care: Quantifying a 20-35% Drop in Healthcare Costs
26:36 Eliminating Friction: Redesigning Employee Benefits Outside Open Enrollment
32:02 Human-First Design and Why AI Will Disrupt Legacy Companies
33:23 The Pandemic Pivot: Turning a Near-Death Event into Wellhub's Evolution
37:27 Advice to His Younger Self and the Best Time to Start a Company
39:45 Closing Thoughts and Sign-Off

Resources:
Subscribe to the AI & The Future of Work Newsletter
Connect with Cesar on LinkedIn
AI Fun Fact
On how one good decision made Thomas Otter (venture capitalist at Acadian Ventures) an accidental HR tech pioneer
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See why Freshworks was named a Leader in the 2026 Gartner® Magic Quadrant™ for ITSM. Learn more → freshworks.com/dant

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Todd Barr is the CEO of Axonis and has spent his career in high growth software infrastructure, living through the shift from Unix to Linux, the rise of DevOps, and the blockchain era before landing in AI. Axonis was built by technical founders with 25 years each in large scale infrastructure across government, defense and intelligence, where sharing the underlying data was never an option. 
Recorded live from the floor of Ai4 2026, this lightning round explores why you do not have to centralize your data to start doing AI, and what it takes to make a decision you can defend later.
Todd and host Dan Turchin dig into what an auditable decision actually records, how governance can live at the data node instead of the application layer, the distance between collecting sensor data and acting on it, and why Todd believes decisions themselves are about to become a category of data.
What You'll Learn
Why centralizing your data is not a prerequisite for AI, and how a federated architecture holds up when nodes go offline and come back
What an auditable decision captures: the data used, the model and its version, the reasoning, and the person who attested to it
How attribute based access control decides what each operator or agent is allowed to see, enforced at the data itself
The sensor to decision gap, and how a flood management team went from raw readings they could not interpret to acting on them in real time
Why collecting data and acting on it are two different problems, and what opens up once that distance closes
What becomes possible once decisions are stored as data, from the cost of each decision to who in the organization decides better
🎙️ Part of our Ai4 2026 compilation series. Listen to the full compilation here: https://www.buzzsprout.com/520474/episodes/19816277  

Resources
Subscribe to the AI & The Future of Work Newsletter
Connect with Todd on LinkedIn

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Daniel Chait is the co-founder and CEO of Greenhouse, the industry-leading hiring software platform designed to help enterprise organizations build fair, structured, and effective recruiting processes. He has been a technology entrepreneur in New York for more than 20 years.

He started Greenhouse about 15 years ago on a simple conviction: companies that follow structured hiring practices get better results, and job seekers deserve a process that is fair and transparent. Today he is leading the company through a reinvention for the AI era, including the acquisition of Ezra AI Labs to bring transparent, conversational AI tools to job seekers and hiring teams alike. 

In this episode, Daniel draws on two decades of building companies where every hire lands directly on the bottom line to ask what candidates and employers both need answered: can AI make hiring more human when it is already making it feel less so?
In this conversation, we discuss:
Why candidates and employers using AI at the same time is creating a doom loop that shuts real humans out.
Why AI-led interviews worry so many job seekers, and what it takes for a conversation with an AI to feel fair.
Why using AI to automatically reject most applicants is tempting, and why Greenhouse said no to itWhy AI-polished resumes are making every candidate look the same, and how hiring can move beyond the resume.
How AI can replicate human bias at light speed, and why Daniel says no vendor should ask you to take their word for it.
What Daniel tells anxious workers, from new grads to senior leaders, about disruption, opportunity, and reinventing a career with AI.

Explore the Conversation
0:00 Welcome Back and This Week's AI Fun Fact
4:48 Meet Daniel Chait, Co-Founder and CEO of Greenhouse
7:55 From a Soulless Consulting Job to Founding a Company
10:43 Reinventing the Applicant Tracking System
15:23 How AI Has Already Reshaped Hiring and Job Seeking
21:11 What the Candid AI Interview Report Reveals About Trust
24:25 Why Auto-Rejecting Candidates With AI Backfires
26:08 Sorting Through the Flood of AI-Generated Applications
30:46 Confronting Bias in AI-Powered Hiring Tools
36:46 Reframing AI Anxiety Into Opportunity
40:11 Time Capsule: Advice to His Younger Self
42:14 Where to Find Greenhouse and Closing Thoughts

Resources
Subscribe to the AI & The Future of Work Newsletter
Connect with Daniel on LinkedIn
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